Bumping an old thread. My chukka boot wearing period has all but come to an end. I have sold all my desert and chukkas. For years I wore them and I almost always felt self conscience wearing them. I always feel hobbit like and I don't know, I just overall felt unoriginal. In any event, I am working back down to the ultimate 5 shoe wardrobe. I have two pairs or Santoni Goodyear top shelf lace ups. Brown sleek cap and black brogue punch cap and I treat them like the children I don't have. I have my 5 year old brown Prada Chelsea boots and random other designer low top sneakers.

Every time I wear my Prada Chelsea boots I receive a compliment and even if I don't receive a verbal compliment, women are always checking them out. You know your shoes are good when an older Upper East Side French lady compliments them. Point is why does this happen? Why did I always wear chukkas and women (including my girlfriend) seemed to hate them? I guess the question I'm really asking is has anyone else noticed an adverse reaction from the opposite sex when wearing either boot? I'm 38, but look very youthful and athletic and 5'9 so I've long wondered if chukkas weren't the right boot for my frame.

I'm very close to pulling the trigger on these and considering I've had tremendous success with my current Chelsea's along with their incredible comfort and ease of use, I can't see how I could go wrong. $500 is a lot, for a casual shoe, however.

Bumping an old thread. My chukka boot wearing period has all but come to an end. I have sold all my desert and chukkas. For years I wore them and I almost always felt self conscience wearing them. I always feel hobbit like and I don't know, I just overall felt unoriginal. In any event, I am working back down to the ultimate 5 shoe wardrobe. I have two pairs or Santoni Goodyear top shelf lace ups. Brown sleek cap and black brogue punch cap and I treat them like the children I don't have. I have my 5 year old brown Prada Chelsea boots and random other designer low top sneakers.

Every time I wear my Prada Chelsea boots I receive a compliment and even if I don't receive a verbal compliment, women are always checking them out. You know your shoes are good when an older Upper East Side French lady compliments them. Point is why does this happen? Why did I always wear chukkas and women (including my girlfriend) seemed to hate them? I guess the question I'm really asking is has anyone else noticed an adverse reaction from the opposite sex when wearing either boot? I'm 38, but look very youthful and athletic and 5'9 so I've long wondered if chukkas weren't the right boot for my frame.

I'm very close to pulling the trigger on these and considering I've had tremendous success with my current Chelsea's along with their incredible comfort and ease of use, I can't see how I could go wrong. $500 is a lot, for a casual shoe, however.

Those are hideous. Old french ladies can have poor judgement; just visit Paris
BTW, for someone of 38 your style musings suggest deeper insecurities. Before
springing for the shoes, I would contact Dr. Drew.

Thanks, Comrade. Your immense value to the Styleforum doesn't go unnoticed. I think we should just contact the moderators or authors of the site right now and ask them to shut it down, since by your logic, my insecurities about "style" require therapy. We'll just delete the 1000's of posts from others who also do not feel comfortable in certain articles of clothing. I see you've got 4,554 posts. I can only imagine the wisdom you've bestowed on others. (Clapping).

As for your comment about the boots, thanks. That's one answer I was looking for.

You know, maybe some ideas on chukkas that I've missed. Maybe a response saying "what type of chukkas were you wearing" or "how about these" or "those boots are not very good looking" or a variety of different things. What I didn't expect was to submit a post with a response that offers therapy as a solution. Some of it was supposed to be tongue and cheek and the fact that you seem to defend or agree with the other poster speaks volume of the value of this forum in general. I'll just shut down the account if that's the case. Thanks.

Just to add to the turmoil, I love Chukkas, have three pairs.
I would have more, if not for the fact that I measure 3EEE-4EEEE
and have trouble finding dress shoes that fit. Here's a model from
Ludwig Reiter. They also have (had) a two eyelet version called
the Autoschuh. Both come in suede too.

Bumping an old thread. My chukka boot wearing period has all but come to an end. I have sold all my desert and chukkas. For years I wore them and I almost always felt self conscience wearing them. I always feel hobbit like and I don't know, I just overall felt unoriginal.

I feel the complete opposite way. I have a pair of black chelsea boots, they fit great, but I feel quite self-conscious wearing them and they just sit in my closet. I don't like the way they look with suits, and they seem too dressy for casual wear.

However, I'm big on chukkas. Love 'em. I have three pair in suede (snuff, dark brown and navy.) They are my go to shoe when I'm not in a suit. I'm on the hunt for a pair in black calf leather with rubber soles, to wear with suits in inclement weather. Not as "formal" as a chelsea, but it's just my preference.

I'm with tim_horton on this, have snuff suede Alden unlined chukkas, brown Herring leather chukkas and black Loake 1880 Chelseas. The Loakes rarely get worn as they are too dressy for jeans and only get an odd outing with a charcoal suit as they are my only black shoes. Both pairs of chukkas on the other hand see lots of action.

Gentle bump because I'm in the midst of finishing my basic wardrobe and shoe collection. The latter has given me much consternation due to a couple of impetuous choices a few years back re: black whole-cuts and dark brown quarter-brogue cap toe oxfords. I'm finally getting use out of the whole-cuts due to wearing them as dress shoes whilst my black oxford cap toes are being re-soled; I haven't really worn the dark brown ones beyond a dozen times because of sizing issues (too big).

Since I bought them, my viewpoint on (dark) brown dress shoes has performed a 180 degree about turn due to Holdfast (goddamn you, you son of a bitch!). I now prefer black dress shoes [oxfords] with suits, period. Brown is for derbies.

In terms of derbies, I have Loake 1880 Cornwall, whose last suits my feet and black monks (Meermin). The latter are my go-to shoes due to having them re-soled a couple of years ago with a dainite sole. Due to the inclement weather, I need another pair of derbies with a dainite sole.

For quite some time, I was convinced that I would never wear boots. I dislike the sleakness of Chelsea boots, the fact that they are slip-ons, and any connotation with the word "Chelsea". Hate the girl's name; hate the area, and especially detest the football team (even more, after the public raping of 11 - make that 10 - grown men on a football field). I didn't think that I would wear an ankle boot (Chukka). It wasn't until I read a couple of threads on building up one's beginning shoe collection, that I started to begin to appreciate the utility and style of the chukka. My previous connotations were some 24/25 years out of date (one of my old school friends who wore something similar in tandem with NAF NAF clothing).

I'm looking more and more towards Loake 1880 Pimlico.

In terms of the actual question to hand, then it has to be the Chukka. Simply because I could never cast a vote for Chelsea - irrespective of the actual question.

For quite some time, I was convinced that I would never wear boots. I dislike the sleakness of Chelsea boots, the fact that they are slip-ons, and any connotation with the word "Chelsea". Hate the girl's name; hate the area, and especially detest the football team (even more, after the public raping of 11 - make that 10 - grown men on a football field).

In terms of the actual question to hand, then it has to be the Chukka. Simply because I could never cast a vote for Chelsea - irrespective of the actual question.

FWIW, some of the earliest versions of chelseas, in the US...circa last quarter 19th century...were called "congress" boots and were very popular in Washington DC and among the "better class" of people.

doubt that will change your mind but if it's just the name that's the issue...

I built myself a pair of wholecut chelseas...er, congress boots... a couple of years ago and although I never thought I would ever like something with elastic in it (cheapens a shoe IMO), I love them. Hassle-free to get on and off, extremely comfortable and look great under dress slacks.